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Bovine Rumen Metabolome Database



Showing metabocard for Sarcosine (RMDB00271)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-09-01 08:19:49
Accession Number RMDB00271
Common Name Sarcosine
Description Sarcosine is the N-methyl derivative of glycine. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase, while glycine-N-methyl transferase generates sarcosine from glycine. Sarcosine is a natural amino acid found in muscles and other body tissues. In the laboratory it may be synthesized from chloroacetic acid and methylamine. Sarcosine is naturally found in the metabolism of choline to glycine. Sarcosine is sweet to the taste and dissolves in water. It is used in manufacturing biodegradable surfactants and toothpastes as well as in other applications. Sarcosine is ubiquitous in biological materials and is present in such foods as egg yolks, turkey, ham, vegetables, legumes, etc. Sarcosine is formed from dietary intake of choline and from the metabolism of methionine, and is rapidly degraded to glycine. Sarcosine has no known toxicity, as evidenced by the lack of phenotypic manifestations of sarcosinemia, an inborn error of sarcosine metabolism. Sarcosinemia can result from severe folate deficiency because of the folate requirement for the conversion of sarcosine to glycine (Wikipedia). Sarcosine has recently been identified as a biomarker for invasive prostate cancer. It was found to be greatly increased during prostate cancer progression to metastasis and could be detected in urine. Sarcosine levels were also increased in invasive prostate cancer cell lines relative to benign prostate epithelial cells.(PMID: 19212411)
Synonyms
  1. (Methylamino)acetate
  2. (Methylamino)acetic acid
  3. (Methylamino)ethanoate
  4. (Methylamino)ethanoic acid
  5. Methylglycine
  6. N-Methylaminoacetate
  7. N-Methylaminoacetic acid
  8. N-Methylglycine
  9. N-methyl-Glycine
  10. Sarcosin
  11. Sarcosinate
  12. Sarcosine
  13. Sarcosinic acid
  14. (methylamino)-Acetate
  15. (methylamino)-Acetic acid
Chemical IUPAC Name 2-methylaminoacetic acid
Chemical Formula C3H7NO2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Quaternary Amines; Amino Acids
Sub Class
  • NA
Family
  • Mammalian_Metabolite
Species
  • secondary amine; secondary aliphatic amine (dialkylamine); carboxylic acid; alpha-aminoacid
Biofunction
  • Component of Glycine, serine and threonine metabolism
Application
Source
  • Endogenous
Average Molecular Weight 89.093
Monoisotopic Molecular Weight 89.047676
Isomeric SMILES CNCC(O)=O
Canonical SMILES CNCC(O)=O
KEGG Compound ID C00213 Link Image
BioCyc ID SARCOSINE Link Image
BiGG ID 34275 Link Image
Wikipedia Link Sarcosine Link Image
METLIN ID 51 Link Image
PubChem Compound 1088 Link Image
PubChem Substance 7994277 Link Image
ChEBI ID 15611 Link Image
CAS Registry Number 107-97-1
InChI Identifier InChI=1/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6)
Synthesis Reference Cipens, G.; Slavinska, V.; Sile, D.; Kreile, D.; Strautina, A.; Krikis, A.; Gutmanis, A. Synthesis of sarcosine and its use. Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija (1986), (5), 515-24.
Melting Point (Experimental) 208 oC
Experimental Water Solubility 300.0 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 308.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity -2.78 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity -3.06 [Predicted by ALOGPS]; -3 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from LogP)
  • Extracellular
  • mitochondria
  • peroxisome
Biofluid Location
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 6.9 +/- 30.53 uM
Age N/A
Sex N/A
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image
Metabolic Enzymes
  1. Peroxisomal sarcosine oxidase
Enzyme 1 [top]
Enzyme 1 ID 895
Enzyme 1 Name Peroxisomal sarcosine oxidase
Enzyme 1 Synonyms
  1. PSO
  2. L-pipecolate oxidase
  3. L-pipecolic acid oxidase
Enzyme 1 Gene Name PIPOX
Enzyme 1 Protein Sequence >Peroxisomal sarcosine oxidase
MAAQRELYDAIVIGAGIQGCFTAYHLAKHSKKVLLLEQFFLPHSRGSSHGQSRIIRRAYP
EDFYTQMMAECYSLWAQLEHEAGTQLYRQTGLLLLGMKENPELKIIQATLSRQGVEHQCL
SSEELKQRFPNIRLARGEVGLLEVSGGVLYADKALRALQDAIRQLGGIVHDGEKVVEIKS
GLPVMVKTTSRSYQAKSLIITAGPWTNRLLRPLGAELPLQTLRINVCYWQEKVPGSYSVS
QAFPCFMGLGLSLAPHHIYGLPSREYPGLMKVCYHHGNNADPEERDCPAAFSDIQDVHIL
SGFVRDHLPDLQPEPAVMEHCMYTNTPDGHFVLDRHPKYDNIVIGAGFSGHGFKLSPVVG
KILYELSMKLTPSYDLTPFRISRFPSLGKAHL
Enzyme 1 Number of Residues 392
Enzyme 1 Molecular Weight 43819.2
Enzyme 1 Theoretical pI 8.05
Enzyme 1 GO Classification
Function
Process
Component
Enzyme 1 General Function Amino acid transport and metabolism
Enzyme 1 Specific Function Metabolizes sarcosine, L-pipecolic acid and L-proline
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 59858253 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q29RU9 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name SOX_BOVIN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1179 bp
ATGGCTGCTCAGAGGGAGCTCTATGACGCCATTGTGATCGGGGCAGGCATCCAGGGCTGC
TTCACGGCGTACCACCTGGCCAAACACAGCAAGAAAGTCCTCCTGCTGGAGCAGTTCTTT
CTCCCGCACTCCCGAGGAAGCTCCCATGGGCAGAGCCGGATCATCCGAAGGGCATACCCA
GAAGATTTCTACACCCAGATGATGGCTGAGTGCTACTCCCTGTGGGCCCAGCTGGAGCAT
GAGGCGGGAACCCAATTATACAGGCAGACTGGACTACTGCTGCTGGGAATGAAGGAGAAC
CCAGAATTAAAGATAATCCAGGCTACTTTGTCGAGGCAGGGAGTGGAGCACCAGTGTCTT
TCATCTGAGGAACTGAAGCAACGTTTCCCCAATATTCGGTTGGCCAGGGGAGAAGTGGGG
CTCTTGGAGGTGTCCGGAGGAGTTCTCTATGCCGACAAGGCACTCAGAGCCCTCCAGGAT
GCAATTCGACAGCTAGGTGGCATAGTGCATGATGGAGAGAAGGTAGTGGAGATAAAATCA
GGGCTACCAGTCATGGTGAAAACTACCTCCAGGAGCTACCAAGCCAAGAGCTTGATCATC
ACGGCAGGTCCTTGGACCAACCGGCTCCTCCGTCCCTTGGGAGCTGAGCTACCTCTCCAG
ACCCTGCGGATCAACGTGTGTTACTGGCAAGAGAAGGTTCCTGGAAGCTACAGTGTGTCC
CAGGCCTTTCCGTGTTTCATGGGCCTGGGCCTCAGCCTGGCTCCTCACCACATCTACGGG
CTGCCCTCCAGAGAGTACCCAGGGCTGATGAAGGTCTGCTATCACCACGGCAACAATGCA
GATCCCGAGGAGCGGGACTGCCCAGCAGCTTTCTCAGACATCCAAGATGTCCACATCCTG
AGCGGTTTTGTCAGAGATCACTTACCTGACCTGCAGCCCGAGCCTGCTGTGATGGAGCAT
TGCATGTACACGAACACCCCCGATGGGCACTTCGTTCTTGATAGACACCCAAAGTACGAC
AACATTGTCATTGGTGCTGGATTCTCTGGGCATGGGTTCAAGTTGTCCCCTGTCGTGGGG
AAGATCCTGTACGAATTAAGCATGAAATTAACGCCATCCTATGACTTGACACCTTTTCGA
ATCAGCCGCTTTCCCAGCCTGGGCAAAGCCCACCTTTGA
Enzyme 1 GenBank Gene ID BT020944 Link Image
Enzyme 1 GeneCard ID PIPOX Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Chromosome:1
Enzyme 1 Locus 17q11.2
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available